<p dir="ltr">Privacy serves as a crucial safeguard for personal autonomy and information, enabling control over personal data and space, fostering trust and security in society, and standing as a cornerstone of democracy by protecting against unwarranted interference. This work aims to enhance Tor, a volunteer-operated network providing privacy to over two million users, by improving its programmability, security, and user-friendliness to support wider adoption and underscore the importance of privacy in protecting individual rights in the digital age.</p><p dir="ltr">Addressing Tor's limitations in adapting to new services and threats, this thesis introduces programmable middleboxes, enabling users to execute complex functions on Tor routers to enhance anonymity, security, and performance. This architecture, called Bento, is designed to secure middleboxes from harmful functions and vice versa, making Tor more flexible and efficient.</p><p dir="ltr">Many of the attacks on Tor's anonymity occur when an adversary can intercept a user’s traffic; it is thus useful to limit how much of a user's traffic can enter potentially adversarial networks. We tackle the vulnerabilities of onion services to surveillance and censorship by proposing DeTor_OS, a Bento function enabling geographic avoidance for onion services- which is challenging since no one entity knows the full circuit between user and onion service, providing a method to circumvent adversarial regions and enhance user privacy.</p><p dir="ltr">The final part focuses on improving onion services' usability and security. Despite their importance, these services face high latency, Denial of Service (DoS) and deanonymization attacks due to their content. We introduce CenTor, a Content Delivery Network (CDN) for onion services using Bento, offering replication, load balancing, and content proximity benefits. Additionally, we enhance performance with multipath routing strategies through uTor, balancing performance and anonymity. We quantitatively analyze how geographical-awareness for an onion service CDN and its clients could impact a user’s anonymity- performance versus security tradeoff. Further, we evaluate CenTor on the live Tor network as well as large-scale Shadow simulations.</p><p dir="ltr">These contributions, requiring no changes to the Tor protocol, represent significant advancements in Tor's capabilities, performance, and defenses, demonstrating potential for immediate benefits to the Tor community.</p>